Sodium Carbonate → HCID 68088706, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl N-tert-butoxycarbonyl-N-[3-[3-(p-tolyl)isoxazol-5-yl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (426 mg, 0.7377 mmol) and 2-bromo-5-isopropylsulfonyl-pyridine (233.8 mg, 0.8852 mmol) in DMF (10 mL) was degassed and placed under an atmosphere of nitrogen. Pd(PPh3)2Cl2 (30.51 mg, 0.07377 mmol) was added and the reaction again degassed. 2M aqueous Na2CO3 (1.106 mL, 2.213 mmol) was added and the reaction was stirred at 95° C. for 2 hours. The reaction mixture was partitioned between EtOAc and brine and the aqueous layer extracted with EtOAc (×3). The combined organic extracts were washed with water (×3) and brine (×2), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 50% EtOAc/Petroleum Ether, loaded in DCM) to give the sub-title product as a yellow solid (344 mg, 74% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.24 (d, J=6.8 Hz, 6H), 1.29 (s, 18H), 2.40 (s, 3H), 3.64 (sept, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.63 (s, 1H), 7.83 (d, J=8.1 Hz, 2H), 8.47 (dd, 1H), 8.58 (d, 1H), 9.12 (d, J=2.2 Hz, 1H), 9.17 (d, 1H) and 9.42 (d, J=2.2 Hz, 1H) ppm; MS (ES+) 635.2.

Provenance & Evidence